Vereenigde Oost Indische Compagnie

Former type	Public company
Industry	Trade
Fate	Bankruptcy
Founded	20 March 1602
Defunct	17 March 1798
Headquarters	East India House, Amsterdam, Holland, Dutch Republic

The shipyard of the Dutch East India Company in Amsterdam, circa 1750.

The Dutch East India Company (Dutch: Vereenigde Oost-Indische Compagnie, VOC, "United East India Company") was a chartered company established in 1602, when the States-General of the Netherlands granted it a 21-year monopoly to carry out colonial activities in Asia. It was the second multinational corporation in the world (the British East India Company was founded two years earlier) and the first company to issue stock. It was also arguably the first megacorporation, possessing quasi-governmental powers, including the ability to wage war, imprison and execute convicts, negotiate treaties, coin money, and establish colonies.
Statistically, the VOC eclipsed all of its rivals in the Asia trade. Between 1602 and 1796 the VOC sent almost a million Europeans to work in the Asia trade on 4,785 ships, and netted for their efforts more than 2.5 million tons of Asian trade goods. By contrast, the rest of Europe combined sent only 882,412 people from 1500 to 1795, and the fleet of the English (later British) East India Company, the VOC’s nearest competitor, was a distant second to its total traffic with 2,690 ships and a mere one-fifth the tonnage of goods carried by the VOC. The VOC enjoyed huge profits from its spice monopoly through most of the 17th century.
Having been set up in 1602, to profit from the Malukan spice trade, in 1619 the VOC established a capital in the port city of Batavia (now Jakarta). Over the next two centuries the Company acquired additional ports as trading bases and safeguarded their interests by taking over surrounding territory. It remained an important trading concern and paid an 18% annual dividend for almost 200 years. Weighed down by corruption in the late 18th century, the Company went bankrupt and was formally dissolved in 1800, its possessions and the debt being taken over by the government of the Dutch Batavian Republic. The VOC's territories became the Dutch East Indies and were expanded over the course of the 19th century to include the whole of the Indonesian archipelago, and in the 20th century would form Indonesia.

History

See also: Dutch East India Company in Indonesia and Economic History of the Netherlands (1500 - 1815)

Background

Company, dating from 7 November 1623, for the amount of 2,400 florins.

During the 16th century, the Spice trade was dominated by the Portuguese who used Lisbon as a staple port. Before the Dutch Revolt, Antwerp had played an important role as a distribution center in northern Europe, but after 1591 the Portuguese used an international syndicate of the German Fuggers and Welsers, and Spanish and Italian firms that used Hamburg as its northern staple, to distribute their goods, thereby cutting out Dutch merchants. At the same time, the Portuguese trade system was unable to supply growing demand, in particular the demand for pepper. The demand for spices was relatively inelastic, and the lagging supply of pepper therefore caused a sharp rise in pepper prices at the time.
Likewise, as Portugal had been "united" with the Spanish crown, with which the Dutch Republic was at war, in 1580, the Portuguese Empire became an appropriate target for military incursions. These three factors formed motive for Dutch merchants to enter the intercontinental spice trade themselves at this time. Finally, a number of Dutchmen like Jan Huyghen van Linschoten and Cornelis de Houtman obtained first hand knowledge of the "secret" Portuguese trade routes and practices, thereby providing opportunity. The stage was thus set for Houtman's four-ship exploratory expedition to Banten, the main pepper port of West Java, where they clashed with both the Portuguese and indigenous Indonesians. Houtman's expedition then sailed east along the north coast of Java, losing twelve crew to a Javanese attack at Sidayu and killing a local ruler in Madura. Half the crew were lost before the expedition made it back to the Netherlands the following year, but with enough spices to make a considerable profit.

In 1598, an increasing number of new fleets were sent out by competing merchant groups from around the Netherlands. Some fleets were lost, but most were successful, with some voyages producing high profits. In March 1599, a fleet of eight ships under Jacob van Neck was the first Dutch fleet to reach the ‘Spice Islands’ of Maluku. The ships returned to Europe in 1599 and 1600 and the expedition made a 400 percent profit. In 1600, the Dutch joined forces with the local Hituese (near Ambon) in an anti-Portuguese alliance, in return for which the Dutch were given the sole right to purchase spices from Hitu. Dutch control of Ambon was achieved in alliance with Hitu when in February 1605, they prepared to attack a Portuguese fort in Ambon but the Portuguese surrendered. In 1613, the Dutch expelled the Portuguese from their Solor fort, but a subsequent Portuguese attack led to a second change of hands; following this second reoccupation, the Dutch once again captured Solor, in 1636. East of Solor on the island of Timor Dutch advances were halted by an autonomous and powerful group of Portuguese Eurasians called the Topasses. They remained in control of the Sandalwood trade and their resistance lasted throughout the 17th and 18th century, causing West Timor to remain under the Portuguese sphere of control.

Formation

At the time, it was customary for a company to be set up only for the duration of a single voyage, and to be liquidated on the return of the fleet. Investment in these expeditions was a very high-risk venture, not only because of the usual dangers of piracy, disease and shipwreck, but also because the interplay of inelastic demand and relatively elastic supplyof spices could make prices tumble at just the wrong            moment, thereby ruining prospects of profitability. To manage such risk the forming of a cartel to control supply would seem logical. This first occurred to the English, who bundled their forces into a monopoly enterprise, the East India Company in 1600, thereby threatening their Dutch competitors with ruin. In 1602, the Dutch government followed suit, sponsoring the creation of a single "United East Indies Company" that was also granted a monopoly over the Asian trade. The charter of the new company empowered it to build forts, maintain armies, and conclude treaties with Asian rulers. It provided for a venture that would continue for 21 years, with a financial accounting only at the end of each decade.

In 1603, the first permanent Dutch trading post in Indonesia was established in Banten, West Java and in 1611, another was established at Jayakarta (later 'Batavia' and then 'Jakarta'). In 1610, the VOC established the post of Governor General to enable firmer control of their affairs in Asia. To advise and control the risk of despotic Governors General, a Council of the Indies (Raad van Indië) was created. The Governor General effectively became the main administrator of the VOC's activities in Asia, although the Heeren XVII, a body of 17 shareholders representing different chambers, continued to officially have overall control.
VOC headquarters were in Ambon for the tenures of the first three Governors General (1610–1619), but it was not a satisfactory location. Although it was at the centre of the spice production areas, it was far from the Asian trade routes and other VOC areas of activity ranging from Africa to Japan. A location in the west of the archipelago was thus sought; the Straits of Malacca were strategic, but had become dangerous following the Portuguese conquest and the first permanent VOC settlement in Banten was controlled by a powerful local ruler and subject to stiff competition from Chinese and English traders.
In 1604, a second English East India Company voyage commanded by Sir Henry Middleton reached the islands of Ternate, Tidore, Ambon and Banda; in Banda, they encountered severe VOC hostility, which saw the beginning of Anglo-Dutch competition for access to spices. From 1611 to 1617, the English established trading posts at Sukadana (southwest Kalimantan), Makassar, Jayakarta and Jepara in Java, and Aceh, Pariaman and Jambi in Sumatra which threatened Dutch ambitions for a monopoly on East Indies trade.^[15] Diplomatic agreements in Europe in 1620 ushered in a period of cooperation between the Dutch and the English over the spice trade. This ended with a notorious, but disputed incident, known as the 'Amboyna massacre', where ten Englishmen were arrested, tried and beheaded for conspiracy against the Dutch government. Although this caused outrage in Europe and a diplomatic crisis, the English quietly withdrew from most of their Indonesian activities (except trading in Bantam) and focused on other Asian interests.

 Growth

Graves of Dutch dignitaries in the ruined St. Paul's Church, Melaka in the former Dutch Malacca

In 1619, Jan Pieterszoon Coen was appointed Governor-General of the VOC. He saw the possibility of the VOC becoming an Asian power, both political and economic. On 30 May 1619, Coen, backed by a force of nineteen ships, stormed Jayakarta driving out the Banten forces; and from the ashes established Batavia as the VOC headquarters. In the 1620s almost the entire native population of the Banda Islands was driven away, starved to death, or killed in an attempt to replace them with Dutch plantations. These plantations were used to grow cloves and nutmeg for export. Coen hoped to settle large numbers of Dutch colonists in the East Indies, but this part of his policies never materialized, mainly because very few Dutch were willing to immigrate to Asia.
Another of Coen's ventures was more successful. A major problem in the European trade with Asia at the time was that the Europeans could offer few goods that Asian consumers wanted, except silver and gold. European traders therefore had to pay for spices with the precious metals, and this was in short supply in Europe, except for Spain and Portugal. The Dutch and English had to obtain it by creating a trade surplus with other European countries. Coen discovered the obvious solution for the problem: to start an intra-Asiatic trade system, whose profits could be used to finance the spice trade with Europe. In the long run this obviated the need for exports of precious metals from Europe, though at first it required the formation of a large trading-capital fund in the Indies. The VOC reinvested a large share of its profits to this end in the period up to 1630. The VOC traded throughout Asia. Ships coming into Batavia from the Netherlands carried supplies for VOC settlements in Asia. Silver and copper from Japan were used to trade with India and China for silk, cotton, porcelain, and textiles. These products were either traded within Asia for the coveted spices or brought back to Europe. The VOC was also instrumental in introducing European ideas and technology to Asia. The Company supported Christian missionaries and traded modern technology with China and Japan. A more peaceful VOC trade post on Dejima, an artificial island off the coast of Nagasaki, was for more than two hundred years the only place where Europeans were permitted to trade with Japan.
In 1640, the VOC obtained the port of Galle, Ceylon, from the Portuguese and broke the latter's monopoly of the cinnamon trade. In 1658, Gerard Pietersz. Hulft laid siege to Colombo, which was captured with the help of King Rajasinghe II of Kandy. By 1659, the Portuguese had been expelled from the coastal regions, which were then occupied by the VOC, securing for it the monopoly over cinnamon. To prevent the Portuguese or the English from ever recapturing Sri Lanka, the VOC went on to conquer the entire Malabar Coast upon the Portuguese, almost entirely driving them from the west coast of India. When news of a peace agreement between Portugal and the Netherlands reached Asia in 1663, Goa was the only remaining Portuguese city on the west coast.

In 1652, Jan van Riebeeck established an outpost at the Cape of Good Hope (the southwestern tip of Africa, currently in South Africa) to re-supply VOC ships on their journey to East Asia. This post later became a full-fledged colony, the Cape Colony, when more Dutch and other Europeans started to settle there.
VOC trading posts were also established in Persia (now Iran), Bengal (now Bangladesh, but then part of India), Malacca (Melaka, now in Malaysia), Siam (now Thailand), mainland China (Canton)^{[verification needed]}, Formosa (now Taiwan) and the Malabar Coast and Coromandel Coast in India. In 1662, however, Koxinga expelled the Dutch from Taiwan (see History of Taiwan).
By 1669, the VOC was the richest private company the world had ever seen, with over 150 merchant ships, 40 warships, 50,000 employees, a private army of 10,000 soldiers, and a dividend payment of 40% on the original investment.
Many of the VOC employees inter-mixed with the indigenous peoples and expanded the Mestizo population of Indos in pre-colonial history

 Reorientation

Around 1670, two events caused the growth of VOC trade to stall. In the first place, the highly profitable trade with Japan started to decline. The loss of the outpost on Formosa to Koxinga and related internal turmoil in China (where the Ming dynasty was being replaced with the Qing dynasty) brought an end to the silk trade after 1666. Though the VOC substituted Bengali for Chinese silk other forces affected the supply of Japanese silver and gold. The shogunate enacted a number of measures to limit the export of these precious metals, in the process limiting VOC opportunities for trade, and severely worsening the terms of trade. Therefore, Japan ceased to function as the lynchpin of the intra-Asiatic trade of the VOC by 1685.
Even more importantly, the Third Anglo-Dutch War temporarily interrupted VOC trade with Europe. This caused a spike in the price of pepper, which enticed the English East India Company (EIC) to aggressively enter this market in the years after 1672. Previously, one of the tenets of the VOC pricing policy was to slightly over-supply the pepper market, so as to depress prices below the level where interlopers were encouraged to enter the market (instead of striving for short-term profit maximization). The wisdom of such a policy was illustrated when a fierce price war with the EIC ensued, as that company flooded the market with new supplies from India. In this struggle for market share, the VOC (which had much larger financial resources) could wait out the EIC. Indeed by 1683, the latter came close to bankruptcy; its share price plummeted from 600 to 250; and its president Josiah Child was temporarily forced from office.
However, the writing was on the wall. Other companies, like the French East India Company and the Danish East India Company also started to make inroads on the Dutch system. The VOC therefore closed the heretofore flourishing open pepper emporium of Bantam by a treaty of 1684 with the Sultan. Also, on the Coromandel Coast, it moved its chief stronghold from Pulicat to Negapatnam, so as to secure a monopoly on the pepper trade at the detriment of the French and the Danes. However, the importance of these traditional commodities in the Asian-European trade was diminishing rapidly at the time. The military outlays that the VOC needed to make to enhance its monopoly were not justified by the increased profits of this declining trade.
Nevertheless, this lesson was slow to sink in and at first the VOC made the strategic decision to improve its military position on the Malabar Coast (hoping thereby to curtail English influence in the area, and end the drain on its resources from the cost of the Malabar garrisons) by using force to compel the Zamorin of Calicut to submit to Dutch domination. In 1710, the Zamorin was made to sign a treaty with the VOC undertaking to trade exclusively with the VOC and expel other European traders. For a brief time, this appeared to improve the Company's prospects. However, in 1715, with EIC encouragement, the Zamorin renounced the treaty. Though a Dutch army managed to suppress this insurrection temporarily, the Zamorin continued to trade with the English and the French, which led to an appreciable upsurge in English and French traffic. The VOC decided in 1721 that it was no longer worth the trouble to try to dominate the Malabar pepper and spice trade. A strategic decision was taken to scale down the Dutch military presence and in effect yield the area to EIC influence.
The 1741 Battle of Colachel by Nairs of Travancore under Raja Marthanda Varma was therefore a rearguard action. The Dutch commander Captain Eustachius De Lannoy was captured. Marthanda Varma agreed to spare the Dutch captain's life on condition that he joined his army and trained his soldiers on modern lines. This defeat in the Travancore-Dutch War is considered the earliest example of an organized Asian power overcoming European military technology and tactics; and it signaled the decline of Dutch power in India.
The attempt to continue as before as a low volume-high profit business enterprise with its core business in the spice trade had therefore failed. The Company had however already (reluctantly) followed the example of its European competitors in diversifying into other Asian commodities, like tea, coffee, cotton, textiles, and sugar. These commodities provided a lower profit margin and therefore required a larger sales volume to generate the same amount of revenue. This structural change in the commodity composition of the VOC's trade started in the early 1680s, after the temporary collapse of the EIC around 1683 offered an excellent opportunity to enter these markets. The actual cause for the change lies, however, in two structural features of this new era.
In the first place, there was a revolutionary change in the tastes affecting European demand for Asian textiles, and coffee and tea, around the turn of the 18th century. Secondly, a new era of an abundant supply of capital at low interest rates suddenly opened around this time. The second factor enabled the Company to easily finance its expansion in the new areas of commerce. Between the 1680s and 1720s, the VOC was therefore able to equip and man an appreciable expansion of its fleet, and acquire a large amount of precious metals to finance the purchase of large amounts of Asian commodities, for shipment to Europe. The overall effect was to approximately double the size of the company.
The tonnage of the returning ships rose by 125 percent in this period. However, the Company's revenues from the sale of goods landed in Europe rose by only 78 percent. This reflects the basic change in the VOC's circumstances that had occurred: it now operated in new markets for goods with an elastic demand, in which it had to compete on an equal footing with other suppliers. This made for low profit margins. Unfortunately, the business information systems of the time made this difficult to discern for the managers of the company, which may partly explain the mistakes they made from hindsight. This lack of information might have been counteracted (as in earlier times in the VOC's history) by the business acumen of the directors. Unfortunately by this time these were almost exclusively recruited from the political regent class, which had long since lost its close relationship with merchant circles.
Low profit margins in themselves don't explain the deterioration of revenues. To a large extent the costs of the operation of the VOC had a "fixed" character (military establishments; maintenance of the fleet and such). Profit levels might therefore have been maintained if the increase in the scale of trading operations that in fact took place, had resulted in economies of scale. However, though larger ships transported the growing volume of goods, labor productivity did not go up sufficiently to realize these. In general the Company's overhead rose in step with the growth in trade volume; declining gross margins translated directly into a decline in profitability of the invested capital. The era of expansion was one of "profitless growth".
Concretely: "[t]he long-term average annual profit in the VOC's 1630-70 'Golden Age' was 2.1 million guilders, of which just under half was distributed as dividends and the remainder reinvested. The long-term average annual profit in the 'Expansion Age' (1680–1730) was 2.0 million guilders, of which three-quarters was distributed as dividend and one-quarter reinvested. In the earlier period, profits averaged 18 percent of total revenues; in the latter period, 10 percent. The annual return of invested capital in the earlier period stood at approximately 6 percent; in the latter period, 3.4 percent."
Nevertheless, in the eyes of investors the VOC did not do too badly. The share price hovered consistently around the 400 mark from the mid-1680s (excepting a hiccup around the Glorious Revolution in 1688), and they reached an all-time high of around 642 in the 1720s. VOC shares then yielded a return of 3.5 percent, only slightly less than the yield on Dutch government bonds.

 Decline

• Engraving of Colombo, circa 1680
• 

  Panorama of Ayutthaya in the Bushuis, Amsterdam
• 

  Kraak porcelain in a museum in Malacca
• 

  The cover of the Hortus Malabaricus by Hendrik Adriaan van Reede tot Drakenstein
• 

  The ship Vryburg on a platter, commissioned 1756
• 

  Anonymous painting with Table Mountain in the background, 1762

However, from there on the fortunes of the VOC started to decline. Five major problems, not all of equal weight, can be adduced to explain its decline in the next fifty years to 1780.

• There was a steady erosion of intra-Asiatic trade by changes in the Asiatic political and economic environment that the VOC could do little about. These factors gradually squeezed the company out of Persia, Suratte, the Malabar Coast, and Bengal. The company had to confine its operations to the belt it physically controlled, from Ceylon through the Indonesian archipelago. The volume of this intra-Asiatic trade, and its profitability, therefore had to shrink.
• The way the company was organized in Asia (centralized on its hub in Batavia) that initially had offered advantages in gathering market information, began to cause disadvantages in the 18th century, because of the inefficiency of first shipping everything to this central point. This disadvantage was most keenly felt in the tea trade, where competitors like the EIC and the Ostend Company shipped directly from China to Europe.
• The "venality" of the VOC's personnel (in the sense of corruption and non-performance of duties), though a problem for all East-India Companies at the time, seems to have plagued the VOC on a larger scale than its competitors. To be sure, the company was not a "good employer". Salaries were low, and "private-account trading" was officially not allowed. Not surprisingly, it proliferated in the 18th century to the detriment of the company's performance. From about the 1790s onward, the phrase perished by corruption (also abbreviated VOC in Dutch) came to summarize the company's future.
• A problem that the VOC shared with other companies was the high mortality and morbidity rates among its employees. This decimated the company's ranks and enervated many of the survivors.
• A self-inflicted wound was the VOC's dividend policy. The dividends distributed by the company had exceeded the surplus it garnered in Europe in every decade but one (1710–1720) from 1690 to 1760. However, in the period up to 1730 the directors shipped resources to Asia to build up the trading capital there. Consolidated bookkeeping therefore probably would have shown that total profits exceeded dividends. In addition, between 1700 and 1740 the company retired 5.4 million guilders of long-term debt. The company therefore was still on a secure financial footing in these years. This changed after 1730. While profits plummeted the bewindhebbers only slightly decreased dividends from the earlier level. Distributed dividends were therefore in excess of earnings in every decade but one (1760–1770). To accomplish this, the Asian capital stock had to be drawn down by 4 million guilders between 1730 and 1780, and the liquid capital available in Europe was reduced by 20 million guilders in the same period. The directors were therefore constrained to replenish the company's liquidity by resorting to short-term financing from anticipatory loans, backed by expected revenues from home-bound fleets.

Despite of all this, the VOC in 1780 remained an enormous operation. Its capital in the Republic, consisting of ships and goods in inventory, totaled 28 million guilders; its capital in Asia, consisting of the liquid trading fund and goods en route to Europe, totaled 46 million guilders. Total capital, net of outstanding debt, stood at 62 million guilders. The prospects of the company at this time therefore need not have been hopeless, had one of the many plans to reform it been taken successfully in hand. However, then the Fourth Anglo-Dutch War intervened. British attacks in Europe and Asia reduced the VOC fleet by half; removed valuable cargo from its control; and devastated its remaining power in Asia. The direct losses of the VOC can be calculated at 43 million guilders. Loans to keep the company operating reduced its net assets to zero.
From 1720 on, the market for sugar from Indonesia declined as the competition from cheap sugar from Brazil increased. European markets became saturated. Dozens of Chinese sugar traders went bankrupt which led to massive unemployment, which in turn led to gangs of unemployed coolies. The Dutch government in Batavia did not adequately respond to these problems. In 1740, rumors of deportation of the gangs from the Batavia area led to widespread rioting. The Dutch military searched houses of Chinese in Batavia searching for weapons. When a house accidentally burnt down, military and impoverished citizens started slaughtering and pillaging the Chinese community. This massacre of the Chinese was deemed sufficiently serious for the board of the VOC to start an official investigation into the Government of the Dutch East Indies for the first time in its history.
After the Fourth Anglo-Dutch War, the VOC was a financial wreck, and after vain attempts by the provincial States of Holland and Zeeland to reorganize it, was nationalised on 1 March 1796 by the new Batavian Republic. Its charter was renewed several times, but allowed to expire on 31 December 1800. Most of the possessions of the former VOC were subsequently occupied by Great Britain during the Napoleonic wars, but after the new United Kingdom of the Netherlands was created by the Congress of Vienna, some of these were restored to this successor state of the old Dutch Republic by the Anglo-Dutch Treaty of 1814.
The Wright family, owners of Voyager Estate in Margaret River Western Australia, acquired the VOC name and trademark in 1995.

 Organization

The VOC had two types of shareholders: the participanten, who could be seen as non-managing partners, and the 76 bewindhebbers (later reduced to 60) who acted as managing partners. This was the usual set-up for Dutch joint-stock companies at the time. The innovation in the case of the VOC was, that the liability of not just the participanten, but also of the bewindhebbers was limited to the paid-in capital (usually, bewindhebbers had unlimited liability). The VOC therefore was a limited-liability company. Also, the capital would be permanent during the lifetime of the company. As a consequence, investors that wished to liquidate their interest in the interim could only do this by selling their share to others on the Amsterdam Stock Exchange.
The VOC consisted of six Chambers (Kamers) in port cities: Amsterdam, Delft, Rotterdam, Enkhuizen, Middelburg and Hoorn. Delegates of these chambers convened as the Heeren XVII (the Lords Seventeen). They were selected from the bewindhebber-class of shareholders.
Of the Heeren XVII, eight delegates were from the Chamber of Amsterdam (one short of a majority on its own), four from the Chamber of Zeeland, and one from each of the smaller Chambers, while the seventeenth seat was alternatively from the Chamber of Zeeland or rotated among the five small Chambers. Amsterdam had thereby the decisive voice. The Zeelanders in particular had misgivings about this arrangement at the beginning. The fear was not unfounded, because in practice it meant Amsterdam stipulated what happened.

Two sides of a duit, a coin minted in 1735 by the VOC.

The six chambers raised the start-up capital of the Dutch East India Company:

Chamber	Capital (Guilders)
Amsterdam	3,679,915
Middelburg	1,300,405
Enkhuizen	540,000
Delft	469,400
Hoorn	266,868
Rotterdam	173,000
Total:	6,424,588

The raising of capital in Rotterdam did not go so smoothly. A considerable part originated from inhabitants of Dordrecht. Although it did not raise as much capital as Amsterdam or Zeeland, Enkhuizen had the largest input in the share capital of the VOC. Under the first 358 shareholders, there were many small entrepreneurs, who dared to take the risk. The minimum investment in the VOC was 3,000 guilders, which priced the Company's stock within the means of many merchants.
Among the early shareholders of the VOC, immigrants played an important role. Under the 1,143 tenderers were 39 Germans and no fewer than 301 from the Southern Netherlands (roughly present Belgium and Luxembourg, then under Habsburg rule), of whom Isaac le Maire was the largest subscriber with ƒ85,000. VOC's total capitalization was ten times that of its British rival.

The logo of the Amsterdam Chamber of the VOC.

The logo of the VOC consisted of a large capital 'V' with an O on the left and a C on the right leg. It appeared on various corporate items, such as cannons and the coin illustrated above. The first letter of the hometown of the chamber conducting the operation was placed on top (see figure for example of the Amsterdam chamber logo). The flag of the company was orange, white, blue (see Dutch flag) with the company logo embroidered on it.
The Heeren XVII (Lords Seventeen) met alternately 6 years in Amsterdam and 2 years in Middelburg. They defined the VOC's general policy and divided the tasks among the Chambers. The Chambers carried out all the necessary work, built their own ships and warehouses and traded the merchandise. The Heeren XVII sent the ships' masters off with extensive instructions on the route to be navigated, prevailing winds, currents, shoals and landmarks. The VOC also produced its own charts.
In the context of the Dutch-Portuguese War the company established its headquarters in Batavia, Java (now Jakarta, Indonesia). Other colonial outposts were also established in the East Indies, such as on the Spice Islands (Moluccas), which include the Banda Islands, where the VOC forcibly maintained a monopoly over nutmeg and mace. Methods used to maintain the monopoly included the violent suppression of the native population, not stopping short of extortion and mass murder.In addition, VOC representatives sometimes used the tactic of burning spice trees in order to force indigenous populations to grow other crops, thus artificially cutting the supply of spices like nutmeg and cloves.

VOC outposts

Organization and leadership structures were varied as necessary in the various VOC outposts:
Opperhoofd is a Dutch word (plural Opperhoofden) which literally means 'supreme head[man]'. In this VOC context, the word is a gubernatorial title, comparable to the English Chief factor, for the chief executive officer of a Dutch factory in the sense of trading post, as led by a Factor, i.e. agent.

See more at VOC Opperhoofden in Japan

 Council of Justice in Batavia

The Council of Justice in Batavia was the appelate court for all the other VOC Company posts in the VOC empire.

Acid

An acid (from the Latin acidus/acēre meaning sour) is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red. Chemicals or substances having the property of an acid are said to be acidic.
Common examples of acids include acetic acid (in vinegar), sulfuric acid (used in car batteries), and tartaric acid (used in baking). As these three examples show, acids can be solutions, liquids, or solids. Gases such as hydrogen chloride can be acids as well. Strong acids and some concentrated weak acids are corrosive, but there are exceptions such as carboranes and boric acid.
There are three common definitions for acids: the Arrhenius definition, the Brønsted-Lowry definition, and the Lewis definition. The Arrhenius definition states that acids are substances which increase the concentration of hydronium ions (H₃O⁺) in solution. The Brønsted-Lowry definition is an expansion: an acid is a substance which can act as a proton donor. Most acids encountered in everyday life are aqueous solutions, or can be dissolved in water, and these two definitions are most relevant. The reason why pHs of acids are less than 7 is that the concentration of hydronium ions is greater than 10⁻⁷ moles per liter. Since pH is defined as the negative logarithm of the concentration of hydronium ions, acids thus have pHs of less than 7. By the Brønsted-Lowry definition, any compound which can easily be deprotonated can be considered an acid. Examples include alcohols and amines which contain O-H or N-H fragments.
In chemistry, the Lewis definition of acidity is frequently encountered. Lewis acids are electron-pair acceptors. Examples of Lewis acids include all metal cations, and electron-deficient molecules such as boron trifluoride and aluminium trichloride. Hydronium ions are acids according to all three definitions. Interestingly, although alcohols and amines can be Brønsted-Lowry acids as mentioned above, they can also function as Lewis bases due to the lone pairs of electrons on their oxygen and nitrogen atoms.

 Definitions and concepts

Modern definitions are concerned with the fundamental chemical reactions common to all acids.

 Arrhenius acids

The Swedish chemist Svante Arrhenius attributed the properties of acidity to hydrogen in 1884. An Arrhenius acid is a substance that increases the concentration of the hydronium ion, H₃O⁺, when dissolved in water. This definition stems from the equilibrium dissociation of water into hydronium and hydroxide (OH⁻) ions:

H₂O(l) + H₂O(l) H₃O⁺(aq) + OH⁻(aq)

In pure water the majority of molecules exist as H₂O, but a small number of molecules are constantly dissociating and re-associating. Pure water is neutral with respect to acidity or basicity because the concentration of hydroxide ions is always equal to the concentration of hydronium ions. An Arrhenius base is a molecule which increases the concentration of the hydroxide ion when dissolved in water. Note that chemists often write H⁺(aq) and refer to the hydrogen ion when describing acid-base reactions but the free hydrogen nucleus, a proton, does not exist alone in water, it exists as the hydronium ion, H₃O⁺ .

 Brønsted-Lowry acids

While the Arrhenius concept is useful for describing many reactions, it is also quite limited in its scope. In 1923 chemists Johannes Nicolaus Brønsted and Thomas Martin Lowry independently recognized that acid-base reactions involve the transfer of a proton. A Brønsted-Lowry acid (or simply Brønsted acid) is a species that donates a proton to a Brønsted-Lowry base. Brønsted-Lowry acid-base theory has several advantages over Arrhenius theory. Consider the following reactions of acetic acid (CH₃COOH), the organic acid that gives vinegar its characteristic taste:

Both theories easily describe the first reaction: CH₃COOH acts as an Arrhenius acid because it acts as a source of H₃O⁺ when dissolved in water, and it acts as a Brønsted acid by donating a proton to water. In the second example CH₃COOH undergoes the same transformation, in this case donating a proton to ammonia (NH₃), but cannot be described using the Arrhenius definition of an acid because the reaction does not produce hydronium. Brønsted-Lowry theory can also be used to describe molecular compounds, whereas Arrhenius acids must be ionic compounds. Hydrogen chloride (HCl) and ammonia combine under several different conditions to form ammonium chloride, NH₄Cl. In aqueous solution HCl behaves as hydrochloric acid and exists as hydronium and chloride ions. The following reactions illustrate the limitations of Arrhenius's definition:

1. H₃O⁺(aq) + Cl⁻(aq) + NH₃ → Cl⁻(aq) + NH₄⁺(aq)
2. HCl(benzene) + NH₃(benzene) → NH₄Cl(s)
3. HCl(g) + NH₃(g) → NH₄Cl(s)

As with the acetic acid reactions, both definitions work for the first example, where water is the solvent and hydronium ion is formed. The next two reactions do not involve the formation of ions but are still proton transfer reactions. In the second reaction hydrogen chloride and ammonia (dissolved in benzene) react to form solid ammonium chloride in a benzene solvent and in the third gaseous HCl and NH₃ combine to form the solid.

 Lewis acids

A third concept was proposed in 1923 by Gilbert N. Lewis which includes reactions with acid-base characteristics that do not involve a proton transfer. A Lewis acid is a species that accepts a pair of electrons from another species; in other words, it is an electron pair acceptor. Brønsted acid-base reactions are proton transfer reactions while Lewis acid-base reactions are electron pair transfers. All Brønsted acids are also Lewis acids, but not all Lewis acids are Brønsted acids. Contrast the following reactions which could be described in terms of acid-base chemistry.

In the first reaction a fluoride ion, F⁻, gives up an electron pair to boron trifluoride to form the product tetrafluoroborate. Fluoride "loses" a pair of valence electrons because the electrons shared in the B—F bond are located in the region of space between the two atomic nuclei and are therefore more distant from the fluoride nucleus than they are in the lone fluoride ion. BF₃ is a Lewis acid because it accepts the electron pair from fluoride. This reaction cannot be described in terms of Brønsted theory because there is no proton transfer. The second reaction can be described using either theory. A proton is transferred from an unspecified Brønsted acid to ammonia, a Brønsted base; alternatively, ammonia acts as a Lewis base and transfers a lone pair of electrons to form a bond with a hydrogen ion. The species that gains the electron pair is the Lewis acid; for example, the oxygen atom in H₃O⁺ gains a pair of electrons when one of the H—O bonds is broken and the electrons shared in the bond become localized on oxygen. Depending on the context, a Lewis acid may also be described as an oxidizer or an electrophile.
The Brønsted-Lowry definition is the most widely used definition; unless otherwise specified acid-base reactions are assumed to involve the transfer of a proton (H⁺) from an acid to a base.

 Dissociation and equilibrium

Reactions of acids are often generalized in the form HA H⁺ + A⁻, where HA represents the acid and A⁻ is the conjugate base. Acid-base conjugate pairs differ by one proton, and can be interconverted by the addition or removal of a proton (protonation and deprotonation, respectively). Note that the acid can be the charged species and the conjugate base can be neutral in which case the generalized reaction scheme could be written as HA⁺ H⁺ + A. In solution there exists an equilibrium between the acid and its conjugate base. The equilibrium constant K is an expression of the equilibrium concentrations of the molecules or the ions in solution. Brackets indicate concentration, such that [H₂O] means the concentration of H₂O. The acid dissociation constant K_a is generally used in the context of acid-base reactions. The numerical value of K_a is equal to the concentration of the products divided by the concentration of the reactants, where the reactant is the acid (HA) and the products are the conjugate base and H⁺.

The stronger of two acids will have a higher K_a than the weaker acid; the ratio of hydrogen ions to acid will be higher for the stronger acid as the stronger acid has a greater tendency to lose its proton. Because the range of possible values for K_a spans many orders of magnitude, a more manageable constant, pK_a is more frequently used, where pK_a = -log₁₀ K_a. Stronger acids have a smaller pK_a than weaker acids. Experimentally determined pK_a at 25°C in aqueous solution are often quoted in textbooks and reference material.

 Nomenclature

In the classical naming system, acids are named according to their anions. That ionic suffix is dropped and replaced with a new suffix (and sometimes prefix), according to the table below. For example, HCl has chloride as its anion, so the -ide suffix makes it take the form hydrochloric acid. In the IUPAC naming system, "aqueous" is simply added to the name of the ionic compound. Thus, for hydrogen chloride, the IUPAC name would be aqueous hydrogen chloride. The prefix "hydro-" is added only if the acid is made up of just hydrogen and one other element.
Classical naming system:

Anion prefix	Anion suffix	Acid prefix	Acid suffix	Example
per	ate	per	ic acid	perchloric acid (HClO4)
	ate		ic acid	chloric acid (HClO3)
	ite		ous acid	chlorous acid (HClO2)
hypo	ite	hypo	ous acid	hypochlorous acid (HClO)
	ide	hydro	ic acid	hydrochloric acid (HCl)

 Acid strength

The strength of an acid refers to its ability or tendency to lose a proton. A strong acid is one that completely dissociates in water; in other words, one mole of a strong acid HA dissolves in water yielding one mole of H⁺ and one mole of the conjugate base, A⁻, and none of the protonated acid HA. In contrast a weak acid only partially dissociates and at equilibrium both the acid and the conjugate base are in solution. Examples of strong acids are hydrochloric acid (HCl), hydroiodic acid (HI), hydrobromic acid (HBr), perchloric acid (HClO₄), nitric acid (HNO₃) and sulfuric acid (H₂SO₄). In water each of these essentially ionizes 100%. The stronger an acid is, the more easily it loses a proton, H⁺. Two key factors that contribute to the ease of deprotonation are the polarity of the H—A bond and the size of atom A, which determines the strength of the H—A bond. Acid strengths are also often discussed in terms of the stability of the conjugate base.
Stronger acids have a larger K_a and a more negative pK_a than weaker acids.
Sulfonic acids, which are organic oxyacids, are a class of strong acids. A common example is toluenesulfonic acid (tosylic acid). Unlike sulfuric acid itself, sulfonic acids can be solids. In fact, polystyrene functionalized into polystyrene sulfonate is a solid strongly acidic plastic that is filterable.
Superacids are acids stronger than 100% sulfuric acid. Examples of superacids are fluoroantimonic acid, magic acid and perchloric acid. Superacids can permanently protonate water to give ionic, crystalline hydronium "salts". They can also quantitatively stabilize carbocations.

 Polarity and the inductive effect

Polarity refers to the distribution of electrons in a bond, the region of space between two atomic nuclei where a pair of electrons is shared. When two atoms have roughly the same electronegativity (ability to attract electrons) the electrons are shared evenly and spend equal time on either end of the bond. When there is a significant difference in electronegativities of two bonded atoms, the electrons spend more time near the nucleus of the more electronegative element and an electrical dipole, or separation of charges, occurs, such that there is a partial negative charge localized on the electronegative element and a partial positive charge on the electropositive element. Hydrogen is an electropositive element and accumulates a slightly positive charge when it is bonded to an electronegative element such as oxygen or bromine. As the electron density on hydrogen decreases it is more easily abstracted, in other words, it is more acidic. Moving from left to right across a row on the periodic table elements become more electronegative (excluding the noble gases), and the strength of the binary acid formed by the element increases accordingly:

Formula	Name	pKa
HF	hydrofluoric acid	3.17
H2O	water	15.7
NH3	ammonia	38
CH4	methane	48

The electronegative element need not be directly bonded to the acidic hydrogen to increase its acidity. An electronegative atom can pull electron density out of an acidic bond through the inductive effect. The electron-withdrawing ability diminishes quickly as the electronegative atom moves away from the acidic bond. The effect is illustrated by the following series of halogenated butanoic acids. Chlorine is more electronegative than bromine and therefore has a stronger effect. The hydrogen atom bonded to the oxygen is the acidic hydrogen. Butanoic acid is a carboxylic acid.

Structure	Name	pKa
	butanoic acid or butyric acid	≈4.8
	4-chlorobutanoic acid	4.5
	3-chlorobutanoic acid	≈4.0
	2-bromobutanoic acid	2.93
	2-chlorobutanoic acid	2.86

As the chlorine atom moves further away from the acidic O—H bond, its effect diminishes. When the chlorine atom is just one carbon removed from the carboxylic acid group the acidity of the compound increases significantly, compared to butanoic acid (a.k.a. butyric acid). However, when the chlorine atom is separated by several bonds the effect is much smaller. Bromine is much more electronegative than either carbon or hydrogen, but not as electronegative as chlorine, so the pK_a of 2-bromobutanoic acid is slightly greater than the pK_a of 2-chlorobutanoic acid.

Perchloric acid (HClO₄) is an oxoacid and a strong acid.

The number of electronegative atoms adjacent an acidic bond also affects acid strength. Oxoacids have the general formula HOX where X can be any atom and may or may not share bonds to other atoms. Increasing the number of electronegative atoms or groups on atom X decreases the electron density in the acidic bond, making the loss of the proton easier. Perchloric acid is a very strong acid (pK_a ≈ -8) and completely dissociates in water. Its chemical formula is HClO₄ and it comprises a central chlorine atom with three chlorine-oxygen double bonds (Cl=O) and one chlorine-oxygen single bond (Cl—O). The singly bonded oxygen bears an extremely acidic hydrogen atom which is easily abstracted. In contrast, chloric acid (HClO₃) is a weaker acid, though still quite strong (pK_a = -1.0), while chlorous acid (HClO₂, pK_a = +2.0) and hypochlorous acid (HClO, pK_a = +7.53) acids are weak acids.
Carboxylic acids are organic acids that contain an acidic hydroxyl group and a carbonyl (C=O bond). Carboxylic acids can be reduced to the corresponding alcohol; the replacement of an electronegative oxygen atom with two electropositive hydrogens yields a product which is essentially non-acidic. The reduction of acetic acid to ethanol using LiAlH₄ (lithium aluminium hydride or LAH) and ether is an example of such a reaction.

The pK_a for ethanol is 16, compared to 4.76 for acetic acid.

 Atomic radius and bond strength

Another factor that contributes to the ability of an acid to lose a proton is the strength of the bond between the acidic hydrogen and the atom that bears it. This, in turn, is dependent on the size of the atoms sharing the bond. For an acid HA, as the size of atom A increases, the strength of the bond decreases, meaning that it is more easily broken, and the strength of the acid increases. Bond strength is a measure of how much energy it takes to break a bond. In other words, it takes less energy to break the bond as atom A grows larger, and the proton is more easily removed by a base. This partially explains why hydrofluoric acid is considered a weak acid while the other hydrohalic acids (HCl, HBr, HI) are strong acids. Although fluorine is more electronegative than the other halogens, its atomic radius is also much smaller, so it shares a stronger bond with hydrogen. Moving down a column on the periodic table atoms become less electronegative but also significantly larger, and the size of the atom tends to dominate its acidity when sharing a bond to hydrogen. Hydrogen sulfide, H₂S, is a stronger acid than water, even though oxygen is more electronegative than sulfur. Just as with the halogens, this is because sulfur is larger than oxygen and the H—S bond is more easily broken than the H—O bond.

 Chemical characteristics

 Monoprotic acids

Monoprotic acids are those acids that are able to donate one proton per molecule during the process of dissociation (sometimes called ionization) as shown below (symbolized by HA):

HA(aq) + H₂O(l) H₃O⁺(aq) + A⁻(aq)         K_a

Common examples of monoprotic acids in mineral acids include hydrochloric acid (HCl) and nitric acid (HNO₃). On the other hand, for organic acids the term mainly indicates the presence of one carboxylic acid group and sometimes these acids are known as monocarboxylic acid. Examples in organic acids include formic acid (HCOOH), acetic acid (CH₃COOH) and benzoic acid (C₆H₅COOH).

See also: Acid dissociation constant#Monoprotic acids

 Polyprotic acids

Polyprotic acids, also known as polybasic acids, are able to donate more than one proton per acid molecule, in contrast to monoprotic acids that only donate one proton per molecule. Specific types of polyprotic acids have more specific names, such as diprotic acid (two potential protons to donate) and triprotic acid (three potential protons to donate).
A diprotic acid (here symbolized by H₂A) can undergo one or two dissociations depending on the pH. Each dissociation has its own dissociation constant, K_a1 and K_a2.

H₂A(aq) + H₂O(l) H₃O⁺(aq) + HA⁻(aq)       K_a1

HA⁻(aq) + H₂O(l) H₃O⁺(aq) + A²⁻(aq)       K_a2

The first dissociation constant is typically greater than the second; i.e., K_a1 > K_a2. For example, sulfuric acid (H₂SO₄) can donate one proton to form the bisulfate anion (HSO₄⁻), for which K_a1 is very large; then it can donate a second proton to form the sulfate anion (SO₄^2-), wherein the K_a2 is intermediate strength. The large K_a1 for the first dissociation makes sulfuric a strong acid. In a similar manner, the weak unstable carbonic acid (H₂CO₃) can lose one proton to form bicarbonate anion (HCO₃⁻) and lose a second to form carbonate anion (CO₃^2-). Both K_a values are small, but K_a1 > K_a2 .
A triprotic acid (H₃A) can undergo one, two, or three dissociations and has three dissociation constants, where K_a1 > K_a2 > K_a3.

H₃A(aq) + H₂O(l) H₃O⁺(aq) + H₂A⁻(aq)        K_a1

H₂A⁻(aq) + H₂O(l) H₃O⁺(aq) + HA²⁻(aq)       K_a2

HA²⁻(aq) + H₂O(l) H₃O⁺(aq) + A³⁻(aq)         K_a3

An inorganic example of a triprotic acid is orthophosphoric acid (H₃PO₄), usually just called phosphoric acid. All three protons can be successively lost to yield H₂PO₄⁻, then HPO₄^2-, and finally PO₄^3-, the orthophosphate ion, usually just called phosphate. An organic example of a triprotic acid is citric acid, which can successively lose three protons to finally form the citrate ion. Even though the positions of the protons on the original molecule may be equivalent, the successive K_a values will differ since it is energetically less favorable to lose a proton if the conjugate base is more negatively charged.
Although the subsequent loss of each hydrogen ion is less favorable, all of the conjugate bases are present in solution. The fractional concentration, α (alpha), for each species can be calculated. For example, a generic diprotic acid will generate 3 species in solution: H₂A, HA^-, and A^2-. The fractional concentrations can be calculated as below when given either the pH (which can be converted to the [H⁺]) or the concentrations of the acid with all its conjugate bases:



A pattern is observed in the above equations and can be expanded to the general n -protic acid that has been deprotonated i -times:
where K₀ = 1 and the other K-terms are the dissociation constants for the acid.

 Neutralization

Hydrochloric acid (in beaker) reacting with ammonia fumes to produce ammonium chloride (white smoke).

Neutralization is the reaction between an acid and a base, producing a salt and neutralized base; for example, hydrochloric acid and sodium hydroxide form sodium chloride and water:

HCl(aq) + NaOH(aq) → H₂O(l) + NaCl(aq)

Neutralization is the basis of titration, where a pH indicator shows equivalence point when the equivalent number of moles of a base have been added to an acid. It is often wrongly assumed that neutralization should result in a solution with pH 7.0, which is only the case with similar acid and base strengths during a reaction.
Neutralization with a base weaker than the acid results in a weakly acidic salt. An example is the weakly acidic ammonium chloride, which is produced from the strong acid hydrogen chloride and the weak base ammonia. Conversely, neutralizing a weak acid with a strong base gives a weakly basic salt, e.g. sodium fluoride from hydrogen fluoride and sodium hydroxide.

 Weak acid/weak base equilibria

Main article: Henderson–Hasselbalch equation

In order to lose a proton, it is necessary that the pH of the system rise above the pK_a of the protonated acid. The decreased concentration of H⁺ in that basic solution shifts the equilibrium towards the conjugate base form (the deprotonated form of the acid). In lower-pH (more acidic) solutions, there is a high enough H⁺ concentration in the solution to cause the acid to remain in its protonated form, or to protonate its conjugate base (the deprotonated form).
Solutions of weak acids and salts of their conjugate bases form buffer solutions.

Applications of acids

There are numerous uses for acids. Acids are often used to remove rust and other corrosion from metals in a process known as pickling. They may be used as an electrolyte in a wet cell battery, such as sulfuric acid in a car battery.
Strong acids, sulfuric acid in particular, are widely used in mineral processing. For example, phosphate minerals react with sulfuric acid to produce phosphoric acid for the production of phosphate fertilizers, and zinc is produced by dissolving zinc oxide into sulfuric acid, purifying the solution and electrowinning.
In the chemical industry, acids react in neutralization reactions to produce salts. For example, nitric acid reacts with ammonia to produce ammonium nitrate, a fertilizer. Additionally, carboxylic acids can be esterified with alcohols, to produce esters.
Acids are used as additives to drinks and foods, as they alter their taste and serve as preservatives. Phosphoric acid, for example, is a component of cola drinks. Acetic acid is used in day to day life as vinegar. Carbonic acid is an important part of some cola drinks and soda. Citric acid is used as a preservative in sauces and pickles.
Tartaric acid is an important component of some commonly used foods like unripened mangoes and tamarind. Natural fruits and vegetables also contain acids. Citric acid is present in oranges, lemon and other citrus fruits. Oxalic acid is present in tomatoes, spinach, and especially in carambola and rhubarb; rhubarb leaves and unripe carambolas are toxic because of high concentrations of oxalic acid.
Ascorbic acid (Vitamin C) is an essential vitamin required in our body and is present in such foods as amla, lemon, citrus fruits, and guava.
Certain acids are used as drugs. Acetylsalicylic acid (Aspirin) is used as a pain killer and for bringing down fevers.
Acids play very important roles in the human body. The hydrochloric acid present in our stomach aids in digestion by breaking down large and complex food molecules. Amino acids are required for synthesis of proteins required for growth and repair of our body tissues. Fatty acids are also required for growth and repair of body tissues. Nucleic acids are important for the manufacturing of DNA, RNA and transmission of characters to offspring through genes. Carbonic acid is important for maintenance of pH equilibrium in the body.

Acid catalysis

Main article: Acid catalysis

Acids are used as catalysts in industrial and organic chemistry; for example, sulfuric acid is used in very large quantities in the alkylation process to produce gasoline. Strong acids, such as sulfuric, phosphoric and hydrochloric acids also effect dehydration and condensation reactions. In biochemistry, many enzymes employ acid catalysis.

 Biological occurrence

Basic structure of an amino acid.

Many biologically important molecules are acids. Nucleic acids, which contain acidic phosphate groups, include DNA and RNA. Nucleic acids contain the genetic code that determines many of an organism's characteristics, and is passed from parents to offspring. DNA contains the chemical blueprint for the synthesis of proteins which are made up of amino acid subunits. Cell membranes contain fatty acid esters such as phospholipids.
An α-amino acid has a central carbon (the α or alpha carbon) which is covalently bonded to a carboxyl group (thus they are carboxylic acids), an amino group, a hydrogen atom and a variable group. The variable group, also called the R group or side chain, determines the identity and many of the properties of a specific amino acid. In glycine, the simplest amino acid, the R group is a hydrogen atom, but in all other amino acids it is contains one or more carbon atoms bonded to hydrogens, and may contain other elements such as sulfur, oxygen or nitrogen. With the exception of glycine, naturally occurring amino acids are chiral and almost invariably occur in the L-configuration. Peptidoglycan, found in some bacterial cell walls contains some D-amino acids. At physiological pH, typically around 7, free amino acids exist in a charged form, where the acidic carboxyl group (-COOH) loses a proton (-COO⁻) and the basic amine group (-NH₂) gains a proton (-NH₃⁺). The entire molecule has a net neutral charge and is a zwitterion, with the exception of amino acids with basic or acidic side chains. Aspartic acid, for example, possesses one protonated amine and two deprotonated carboxyl groups, for a net charge of -1 at physiological pH.
Fatty acids and fatty acid derivatives are another group of carboxylic acids that play a significant role in biology. These contain long hydrocarbon chains and a carboxylic acid group on one end. The cell membrane of nearly all organisms is primarily made up of a phospholipid bilayer, a micelle of hydrophobic fatty acid esters with polar, hydrophilic phosphate "head" groups. Membranes contain additional components, some of which can participate in acid-base reactions.
In humans and many other animals, hydrochloric acid is a part of the gastric acid secreted within the stomach to help hydrolyze proteins and polysaccharides, as well as converting the inactive pro-enzyme, pepsinogen into the enzyme, pepsin. Some organisms produce acids for defense; for example, ants produce formic acid.
Acid-base equilibrium plays a critical role in regulating mammalian breathing. Oxygen gas (O₂) drives cellular respiration, the process by which animals release the chemical potential energy stored in food, producing carbon dioxide (CO₂) as a byproduct. Oxygen and carbon dioxide are exchanged in the lungs, and the body responds to changing energy demands by adjusting the rate of ventilation. For example, during periods of exertion the body rapidly breaks down stored carbohydrates and fat, releasing CO₂ into the blood stream. In aqueous solutions such as blood CO₂ exists in equilibrium with carbonic acid and bicarbonate ion.

CO₂ + H₂O H₂CO₃ H⁺ + HCO₃⁻

It is the decrease in pH that signals the brain to breath faster and deeper, expelling the excess CO₂ and resupplying the cells with O₂.

Aspirin (acetylsalicylic acid) is a carboxylic acid.

Cell membranes are generally impermeable to charged or large, polar molecules because of the lipophilic fatty acyl chains comprising their interior. Many biologically important molecules, including a number of pharmaceutical agents, are organic weak acids which can cross the membrane in their protonated, uncharged form but not in their charged form (i.e. as the conjugate base). For this reason the activity of many drugs can be enhanced or inhibited by the use of antacids or acidic foods. The charged form, however, is often more soluble in blood and cytosol, both aqueous environments. When the extracellular environment is more acidic than the neutral pH within the cell, certain acids will exist in their neutral form and will be membrane soluble, allowing them to cross the phospholipid bilayer. Acids that lose a proton at the intracellular pH will exist in their soluble, charged form and are thus able to diffuse through the cytosol to their target. Ibuprofen, aspirin and penicillin are examples of drugs that are weak acids.